Something isn't right, for some reason my monitor keeps displaying that my footage is offline while it clearly isn't. I've tried exporting the clip anyways and the video has that same offline screen while the audio is just fine. What is going on here?

Well, for starters you're using .wmv files. They're generally used for final delivery, not what you start with. It could be that Premiere is 'working with' the media, preparing it for use, and you just have to wait till it's finished before you work.